Advertisement

Chemistry of Heterocyclic Compounds

, Volume 27, Issue 2, pp 135–139 | Cite as

Use of two-dimensional spectroscopy for the determination of the stereochemical structure of 3-carbethoxy-2-methyl-7a-(4-carbethoxy-5-methyl-2-furyl)-3a,4,5,6,7,7a-hexahydrobenzofuran

  • V. A. Chertkov
  • G. G. Melikyan
  • A. B. Sargsyan
  • Sh. O. Badanyan
Article
  • 30 Downloads

Abstract

Homo- and heteronuclear two-dimensional correlation spectra, as well as J-resolved spectra with selective excitation, were used to analyze in detail the stereochemical structure of 3-carbethoxy-2-methyl-7a-(4-carbethoxy-5-methyl-2-furyl)-3a,4,5,6,7,7a-hexahydrobenzofuran, obtained by the reaction of cyclohexenyl-acetylene with acetoacetic ester in the presence of a manganese(III) salt. It was shown that the use of the long-range 13C-1H coupling constants is a very effective method for the determination of the conformation of the molecule. The stereochemical aspects of the reaction of cyclohexenylacetylene with acetoacetic ester is discussed.

Keywords

Spectroscopy Ester Manganese Organic Chemistry Correlation Spectrum 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    G. G. Melikyan, D. A. Mkrtchyan, and Sh. O. Badanyan, Khim. Geterotsikl. Soedin., No. 7, 884 (1980).Google Scholar
  2. 2.
    G. G. Melikyan, D. A. Mkrtchyan, and Sh. O. Badanyan, Khim. Geterotsikl. Soedin., No. 1, 19 (1982).Google Scholar
  3. 3.
    G. G. Melikyan, D. A. Mkrtchyan, V. M. Mkrtchyan, and Sh. O. Badanyan, Khim. Geterotsikl. Soedin., No. 3, 308 (1985).Google Scholar
  4. 4.
    G. G. Melikyan, A. B. Sargsyan, V. S. Giri, R. T. Grigoryan, and Sh. O. Badanyan, Khim. Geterotsikl. Soedin., No. 3, 317 (1988).Google Scholar
  5. 5.
    Sh. O. Badanyan, G. G. Melikyan, and D. A. Mkrtchyan, Usp. Khim., 58, 475 (1989).Google Scholar
  6. 6.
    W. E. Fristad and J. R. Peterson, J. Org. Chem., 51, 10 (1985).Google Scholar
  7. 7.
    K. Witkiewicz and Z. Chahudzinski, Roczn. Chem., 51, 2155 (1977).Google Scholar
  8. 8.
    N. Ito, H. Nishino, and K. Kurosawa, Bull. Chem. Soc. Jpn., 56, 3527 (1983).Google Scholar
  9. 9.
    M. G. Vinogradov, M. S. Pogosyan, A. Ya. Shteinshneider, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 842 (1983).Google Scholar
  10. 10.
    N. M. Sergeev and O. A. Subbotin, Usp. Khim., 47, 477 (1978).Google Scholar
  11. 11.
    E. W. Garbish and M. C. Griffith, J. Am. Chem. Soc., 90, 6543 (1968).Google Scholar
  12. 12.
    V. R. Haddon and L. M. Jackman, Org. Magn. Reson., 5, 333 (1973).Google Scholar
  13. 13.
    D. Hoffner, S. Lesko, and G. Binsch, Org. Magn. Reson., 11, 179 (1978).Google Scholar
  14. 14.
    V. A. Chertkov and N. M. Sergeyev, J. Am. Chem. Soc., 99, 6750 (1977).Google Scholar
  15. 15.
    P. E. Hansen, Progress in NMR Spectroscopy, Vol. 14 (1981), p. 175.Google Scholar
  16. 16.
    A. Bax and R. Freeman, J. Am. Chem. Soc., 104, 1099 (1982).Google Scholar
  17. 17.
    M. Hansen, R. S. Hansen, and H. J. Jacobsen, J. Magn. Reson., 13, 386 (1974).Google Scholar
  18. 18.
    A. Bax, Two-Dimensional NMR in Liquids, Delft Univ. Press, Dordrecht (1984).Google Scholar
  19. 19.
    R. R. Ernst, G. Bodenhausen, and A. Wokaun, Principles of NMR in One and Two Dimensions, Clarendon Press, Oxford (1987).Google Scholar
  20. 20.
    D. Nonkhibel and Dz. Yolton, Chemistry of Free Radicals [Russian translation], Mir, Moscow (1977).Google Scholar
  21. 21.
    O. S. Ten, J. Am. Chem. Soc., 91, 144 (1969).Google Scholar
  22. 22.
    J. Hine, J. Am. Chem. Soc., 88, 5525 (1966).Google Scholar
  23. 23.
    E. Eliel, H. Allindzher, S. Enzhial, and G. Morrison, Conformational Analysis [Russian translation], Mir, Moscow (1969).Google Scholar

Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • V. A. Chertkov
    • 1
    • 2
  • G. G. Melikyan
    • 1
    • 2
  • A. B. Sargsyan
    • 1
    • 2
  • Sh. O. Badanyan
    • 1
    • 2
  1. 1.M. V. Lomonosov Moscow State UniversityUSSR
  2. 2.Institute of Organic ChemistryAcademy of Sciences of the Armenian SSRErevan

Personalised recommendations